JP6223824B2 - 新規な自己反応性アーム及び同物を含むプロドラッグ - Google Patents
新規な自己反応性アーム及び同物を含むプロドラッグ Download PDFInfo
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- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
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- A61K47/55—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound the modifying agent being also a pharmacologically or therapeutically active agent, i.e. the entire conjugate being a codrug, i.e. a dimer, oligomer or polymer of pharmacologically or therapeutically active compounds
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C07C205/21—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C205/22—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having one nitro groups bound to the ring
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
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Description
ここで
- Xは、OH、NH2、NHOH、又はR’NHであってよく、ここでR’は、線状又は分枝状の、飽和又は不飽和のC1〜C10アルキル基であってよく、
- Yは、H又は電子求引性基であり、特にはNO2、CF3、又はハロゲンから選ばれてよく、
- R1及びR2は互に独立に、H又は線状若しくは分枝状の、飽和若しくは不飽和のC1〜C10アルキル基であってよく、
- Fは、クリックケミストリーによって活性化可能な反応性官能基であってよく、特には-C≡CR'''、-N3、-SH、-C=CH2、シクロオクチン、マレイミド、-SO2N3、又は-COSR'''から選ばれるものであってよく、ここでR'''はH又は線状若しくは分枝状の、飽和若しくは不飽和のC1〜C10アルキル基である。
ここで、
- Y、R1及びR2は、前に定義されたとおりであり、
- X’ は、O、NH、NOH、R’Nであってよく、ここでR’は前に定義されたとおりであり、
- Eは、カルボキシル基又はエーテル結合によってX'に結合された不安定基であってよく、
- Aは、O、S、NH、NR"であってよく、ここでR"は線状又は分枝状の、飽和又は不飽和のC1〜C10アルキル基であり、好ましくはNHであってよく、
- Dは、治療又は診断において使用可能な活性化合物であってよく、
- n = 0又は1であり、且つZは、O又はNから選ばれる1又はそれより多いヘテロ原子により中断されていてもよい、線状又は分枝状の、飽和又は不飽和のC1〜C10アルキレン基、グリコシル基、O-(CHR3-CHR4-O-)m又はN-(CHR3-CHR4-O-)m 基、ここでmは1〜20の自然整数であり、R3及びR4は互に独立に、H又はCH3であり、ただしR3及びR4は同時にはCH3でない、アミノ酸若しくはペプチドに由来する基、又はそれらの組み合わせであってよく、
- Lは、ペプチド、タンパク質、抗体若しくは抗原を認識する抗体断片、細胞受容体のリガンド、バイオポリマー、単糖、オリゴ糖、ホルモン、ビタミン、デンドリマー、ポリアミン、又はナノパーティクルから選ばれるターゲティングリガンドでありうる、
- Gは、F基(前に定義されたとおりのもの)とx-(Z)n-L基との間のクリックケミストリー反応から結果する基であり、ここでZ及びLは上記で定義されたとおりであり、且つ、xは、クリックケミストリーにより活性化可能であり且つFと反応することができる反応性官能基である。
- Xは、OH、NH2、NHOH、又はR’NHであってよく、ここでR’は線状又は分枝状の、飽和又は不飽和のC1〜C10アルキル基でありうる、
- Yは、H又は電子求引性基であってよく、特にはNO2、CF3、又はハロゲンから選ばれる、
- R1及びR2は互に独立に、H又は線状若しくは分枝状の、飽和若しくは不飽和のC1〜C10アルキル基でありうる、
- Fは、クリックケミストリーにより活性化可能な反応性官能基でありうる。
- Y、R1、及びR2は前に定義されたとおりであってよく、
- X’はO、NH、NOH、R’Nであってよく、ここでR’は前に定義されたとおりであり、
- Eはカルボキシル基又はエーテル結合によってX'に結合された不安定基であってよく、
- AはO、S、NH、NR"であってよく、ここでR"は線状又は分枝状の、飽和又は不飽和のC1〜C10アルキル基であり、好ましくはNHでありうる、
- Dは、治療又は診断において使用可能な活性な化合物であってよく、
- n = 0又は1であり、且つ、Zは線状又は分枝状の、飽和又は不飽和の、O又はNから選択された1又はそれより多くの(1以上の)ヘテロ原子により中断されていてもよい、C1-C10アルキレン基、グリコシル基、O-(CHR3-CHR4-O-)m又はN-(CHR3-CHR4-O-)m基、ここでmは1〜20の自然整数であり、R3及びR4は互いに独立にH又はCH3であり、ただしR3及びR4は同時にはCH3でない、アミノ酸又はペプチドに由来する基、又はそれらの組み合わせでありうる、
- Lは、ペプチド、タンパク質、抗体又は抗原認識性抗体断片、細胞受容体のリガンド、バイオポリマー、単糖、オリゴ糖、ホルモン、ビタミン、デンドリマー、ポリアミン又はナノパーティクルから選ばれるターゲティングリガンドでありうる、
- Gは、F基(前に定義されたとおりのもの)とx-(Z)n-L基(ここでZ及びLは上で定義されたとおりであり且つxはクリックケミストリーにより活性化可能であり且つFと反応することができる反応性官能基である)との間のクリックケミストリー反応から結果する基である、
又はその医薬的に許容できる塩でありうる。
ここで
- pは 0〜3、好ましくは1〜2、の自然整数であってよく、さらにより好ましくはpは0、1、又は2である、
- Qは、-NH2又は-OHであってよく、好ましくは-NH2である、
- 各Q’は、互に独立に、NH又はOであってよく、好ましくはNHである、
- R5及びR6は、互に独立に、H又は-CH2OR9であってよく、ここでR9は、以下で定義されるとおりのR7又はR8でありうる、
- R7及びR8は、互に独立に、H又は以下の一般式(IV)を有するサブユニットであってよく:
- #は、ベンジル酸素との結合を表し、
- qは、0〜3、好ましくは1〜2、の自然整数であってよく、さらにより好ましくはqは0、1、又は2である、
- Q’は、上記で定義されたとおりであり、
- R10は、上記で定義されたとおりのR5又はR6であってよく、且つ
- R11は、上記で定義されたとおりのR7又はR8でありうる。
ここで、
- Q’及びpは上記で定義されたとおりであり、
- *は、一般式(II)に関して定義されたとおりのAとの結合を表し、
- R12及びR13は、互に独立に、H又は-CH2OD’であってよく、ここでD’は以下で定義されたとおりのものであり、且つ
- D’は、上記で定義されたとおりの活性化合物又は以下の一般式(VI)を有する化合物を表してよく、
- #、Q’、D’、及びqは、上記で定義されたとおりであり、
- R14は、H又は-CH2OD’であってよく、D’は上記で定義されたとおりである。
a-一般式(I)又は(Ia)を有する化合物を化合物E-wと反応させること、
b- 工程a-の反応産物を化合物D-vと反応させること、そして
c- 工程b-の反応産物を化合物L-(Z)n-と反応させること、
からなる工程を少なくとも含んでよく、
ここで、一般式(I)又は(Ia)を有する化合物、E-w、D-v、及びL-(Z)n-は、特には以下で定義されたとおりでる。
Claims (3)
- XがOHであり、Yが、NO2であり且つXに対してオルト位にあり、R1及びR2がHであり、及びFが、-C≡CHである、請求項1に記載の化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1053921 | 2010-05-20 | ||
FR1053921A FR2960153B1 (fr) | 2010-05-20 | 2010-05-20 | Nouveaux bras autoreactifs et prodrogues les comprenant |
PCT/IB2011/052184 WO2011145068A1 (fr) | 2010-05-20 | 2011-05-18 | Nouveaux bras autoréactifs et prodrogues les comprenant |
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JP2013532132A JP2013532132A (ja) | 2013-08-15 |
JP2013532132A5 JP2013532132A5 (ja) | 2014-06-26 |
JP6223824B2 true JP6223824B2 (ja) | 2017-11-01 |
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JP2013510716A Active JP6223824B2 (ja) | 2010-05-20 | 2011-05-18 | 新規な自己反応性アーム及び同物を含むプロドラッグ |
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US (1) | US9000135B2 (ja) |
EP (1) | EP2571528B1 (ja) |
JP (1) | JP6223824B2 (ja) |
CA (1) | CA2799773C (ja) |
ES (1) | ES2666562T3 (ja) |
FR (1) | FR2960153B1 (ja) |
WO (1) | WO2011145068A1 (ja) |
Families Citing this family (18)
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FR3017298B1 (fr) * | 2014-02-07 | 2016-03-04 | Centre Nat Rech Scient | Conjugues et pro-drogues pour le traitement du cancer et de maladies inflammatoires |
KR101628872B1 (ko) | 2014-05-28 | 2016-06-09 | 주식회사 레고켐 바이오사이언스 | 자가-희생 기를 포함하는 화합물 |
US10973920B2 (en) | 2014-06-30 | 2021-04-13 | Glykos Finland Oy | Saccharide derivative of a toxic payload and antibody conjugates thereof |
WO2016144814A1 (en) * | 2015-03-06 | 2016-09-15 | Colorado State University Research Foundation | Synthesis and utility of new capgroup largazole analogs |
KR102368068B1 (ko) | 2015-08-24 | 2022-02-25 | 삼성전자주식회사 | 반도체 소자 제조용 조성물 및 이를 이용하는 반도체 소자의 제조 방법 |
CN107847606A (zh) | 2015-11-25 | 2018-03-27 | 乐高化学生物科学股份有限公司 | 包含自降解基团的缀合物及其相关方法 |
EP3380126A4 (en) * | 2015-11-25 | 2019-07-24 | LegoChem Biosciences, Inc. | ANTIBODY-MEDICINAL CONJUGATES COMPRISING BRANCHED LINKS AND RELATED METHODS |
CA3006247A1 (en) | 2015-11-25 | 2017-06-01 | Legochem Biosciences, Inc. | Conjugates comprising peptide groups and methods related thereto |
KR102085798B1 (ko) | 2016-12-28 | 2020-03-06 | 주식회사 인투셀 | 베타-갈락토사이드가 도입된 자가-희생 기를 포함하는 화합물 |
BR112019020136A2 (pt) | 2017-03-29 | 2020-04-22 | Legochem Biosciences Inc | profármaco de dímero de pirrolobenzodiazepina e composto de conjugado ligando-ligante do mesmo |
EP3624854A1 (en) | 2017-05-16 | 2020-03-25 | Université de Strasbourg | Protein-drug conjugates and their use in the treatment of cancers |
MX2020010201A (es) * | 2018-04-03 | 2020-12-10 | Syndivia | Conjugado de farmaco citotoxico y forma de profarmaco de dicho conjugado. |
CA3099680A1 (en) | 2018-05-09 | 2019-11-14 | Legochem Biosciences, Inc. | Compositions and methods related to anti-cd19 antibody drug conjugates |
KR102258299B1 (ko) * | 2019-03-21 | 2021-05-28 | 고려대학교 산학협력단 | 대장암 선택적 항암 치료진단제 |
KR20210028544A (ko) | 2019-09-04 | 2021-03-12 | 주식회사 레고켐 바이오사이언스 | 인간 ror1에 대한 항체를 포함하는 항체 약물 접합체 및 이의 용도 |
EP4274619A1 (en) * | 2021-01-08 | 2023-11-15 | Lycia Therapeutics, Inc. | Bifunctional folate receptor binding compounds |
EP4313157A1 (en) | 2021-03-30 | 2024-02-07 | Mablink Bioscience | Enzyme-triggered self-reacting linker having improved physicochemical and pharmacological properties |
FR3126982B1 (fr) | 2021-09-14 | 2023-09-15 | Centre Nat Rech Scient | Vecteurs ciblant la beta-d-n-acetylglucosaminidase |
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WO1981001145A1 (en) | 1979-10-18 | 1981-04-30 | Univ Illinois | Hydrolytic enzyme-activatible pro-drugs |
US4379166A (en) * | 1981-08-03 | 1983-04-05 | Schering Corporation | Arylmethoxy-, arylmethylthio-, heteroarylmethoxy-, and heteroarylmethylthio-alkylaminoalcohols |
CH682322A5 (ja) * | 1990-06-05 | 1993-08-31 | Glaxo Group Ltd | |
FR2676058B1 (fr) * | 1991-04-30 | 1994-02-25 | Hoechst Lab | Prodrogues glycosylees, leur procede de preparation et leur utilisation dans le traitement des cancers. |
EP0647450A1 (en) * | 1993-09-09 | 1995-04-12 | BEHRINGWERKE Aktiengesellschaft | Improved prodrugs for enzyme mediated activation |
SI0769967T1 (sl) * | 1994-08-19 | 2008-06-30 | Wallone Region | Konjugati vsebujoäśi protitumorna sredstva in njihova uporaba |
FR2852606A1 (fr) * | 2003-03-18 | 2004-09-24 | Inst Nat Sante Rech Med | Moyens pour inhiber simultanement l'expression de plusieurs genes impliques dans une pathologie |
US20060088475A1 (en) * | 2004-05-10 | 2006-04-27 | Northwestern University | Self-immolative magnetic resonance imaging contrast agents sensitive to beta-glucuronidase |
EP2098533A1 (en) | 2008-03-07 | 2009-09-09 | Pharmachemie B.V. | Esters of glucuronide prodrugs of anthracyclines and method of preparation and use in tumor-selective chemotherapy |
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2010
- 2010-05-20 FR FR1053921A patent/FR2960153B1/fr not_active Expired - Fee Related
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2011
- 2011-05-18 CA CA2799773A patent/CA2799773C/fr active Active
- 2011-05-18 ES ES11724800.5T patent/ES2666562T3/es active Active
- 2011-05-18 EP EP11724800.5A patent/EP2571528B1/fr active Active
- 2011-05-18 JP JP2013510716A patent/JP6223824B2/ja active Active
- 2011-05-18 WO PCT/IB2011/052184 patent/WO2011145068A1/fr active Application Filing
- 2011-05-18 US US13/699,173 patent/US9000135B2/en active Active
Also Published As
Publication number | Publication date |
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CA2799773C (fr) | 2019-10-22 |
EP2571528B1 (fr) | 2018-01-31 |
FR2960153B1 (fr) | 2012-08-17 |
CA2799773A1 (fr) | 2011-11-24 |
EP2571528A1 (fr) | 2013-03-27 |
JP2013532132A (ja) | 2013-08-15 |
US20130144045A1 (en) | 2013-06-06 |
ES2666562T3 (es) | 2018-05-07 |
US9000135B2 (en) | 2015-04-07 |
WO2011145068A1 (fr) | 2011-11-24 |
FR2960153A1 (fr) | 2011-11-25 |
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